The Joy of Missing Out

What Portugal, a Potato Vendor, and a Week of Adventure Taught Me About Patience and Persistence

“Life moves pretty fast. If you don't stop and look around once in a while, you could miss it.” - Ferris Bueller, Ferris Bueller's Day Off (1986)

His worn leather shoes had memorized the cobblestones of Zambujeira do Mar. We'd just finished a twenty-five-kilometer bike ride through the cork forests when I pulled up to find a weathered pickup truck already parked on the village's narrow main street. The old man was deep in his rhythm, jacket draped across his left shoulder as a cushion, potato sack settling into that practiced groove.

Watching him brought two truths into sharp focus: real success is rhythm, and clarity comes from stepping away.

Up the stairs. Back to the truck. Another sack. Down again. Never stopping.

As our group arrived from the morning's ride, bikes accumulated around his truck like metal obstacles. He simply adapted. Same rhythm, same pace, but now weaving between handlebars and wheels with fluid efficiency. Each loop became a navigation puzzle, but the essential work never stopped.

Twenty minutes later, when we departed for the second part of the ride, he was still at it. Still carrying sacks. Still climbing stairs. We'd witnessed just a slice of his day, but he'd shown us something most people never grasp: real achievement comes from doing the work, trip after trip, regardless of audience or obstacles.

This wasn't the vacation insight I'd expected.

We'd spent five years building Sugar Capital, and with our first distribution behind us and Fund III's first close coming in July, I figured I'd earned the right to perfect horizontal relaxation. My vacation formula was elegantly simple: sun, pool, drink, repeat. Why trade poolside perfection for sweaty bike rides, hikes, and kayaking?

The Backroads (A++, highly recommend) active family trip struck me as elaborate torture disguised as vacation. Our friends had done this before and insisted we'd love it. Lisa trusted their judgment, I grudgingly agreed, anticipating a week of forced enthusiasm and camp-counselor energy.

Instead, I discovered something I'd forgotten: the electric thrill of genuine adventure mixed with meeting strangers who quickly became friends. It felt like summer camp for families, which initially triggered every instinct to flee. But something magical happens when you strip away familiar work rhythms and submit to entirely new experiences alongside Katie, Juliet, and Elle.

The revelation came from stepping back from constant urgency. Sure, I checked in periodically, even dialed into one call that mercifully had terrible connection and forced me off quickly. But for the first time in years, I experienced what our guide called "JOMO" (the joy of missing out).

Distance provides clarity that proximity obscures. Removed from daily work urgency, patterns emerged with startling precision. Problems that once felt massive shrank to their proper size when measured against Atlantic horizons. Strategy questions I'd been wrestling with around Fund III (portfolio construction, LP relationships, team expansion) suddenly had obvious answers when viewed from Portuguese hillsides. Solutions that had eluded me crystallized while kayaking through sea caves.

This isn't vacation therapy nonsense. It's practical reality. Your mind needs space to work properly. When you're always plugged in, always responding, always deciding, you lose perspective. You mistake motion for progress.

Each day reinforced this truth. We pedaled through cork forests together, kayaked through sea caves as a group, some tried surfing, and discovered that shared adventures create the strongest bonds regardless of age.

Our evenings became laboratories for connection. At a rustic adega, adults sampled Portugal's distinctive wines while children devoured pastéis de nata, their faces sticky with custard and joy. Those custard tarts became our obsession (rating them at every stop like pizza, "One Bite! Everyone knows the rules!").

Later, in the fishing village of Arrifana, I watched my close friend courageously sample barnacles for the first time. It was a moment of cultural bravery that reminded me why I invest in people willing to try the unthinkable, even as my seafood aversion kept me safely focused on bread and wine.

The most powerful moments came during quiet evening hours at our nature retreat, watching our families forge new friendships with fellow travelers. Complete strangers became allies through shared adventures, showing how real connections happen fastest when we step out of familiar roles.

The potato vendor never knew he was providing business education. His methodical work, that carefully positioned jacket, those deliberate steps around our accumulating bikes: all of it embodied those two fundamental truths.

First: sustainable success requires consistency maintained regardless of changing conditions. The people who endure understand that meaningful achievement unfolds over years, not quarters. They find ways to protect themselves for the long journey while never stopping the essential work, even when the world places new obstacles in their path.

Second: watching him taught me what I'd forgotten about stepping away to see clearly. He wasn't consciously demonstrating some leadership principle. He was just doing his job. But observing his steady rhythm from my forced break made me realize something most miss. Sometimes the most productive thing you can do is stop being productive.

Portugal taught me that adventure beats leisure, that the rhythm of worn shoes on stone contains more wisdom than any business book, and that stepping away from work isn't indulgence. It's necessity.

As Sugar Capital enters its sixth year, I'm reminded that patience isn't just virtue. It's competitive advantage. The people who win are the ones willing to maintain their rhythm indefinitely, carrying their load, trusting that persistence compounds into something extraordinary.

I can't shake the image of that old man: his worn shoes on ancient stone, his unbroken rhythm, his quiet mastery of doing the work that matters.

That's the real lesson: greatness doesn't live in always-on or "I out-hustle you" bravado. It lives in the rhythm. The ritual. The refusal to rush. It lives in knowing when to step away long enough to see what truly deserves your energy.

Work will always wait.

Wisdom won't.

Sometimes the joy is in missing out.